WO2005052027A1 - Composes arylamine reticulables et oligomeres conjugues de polymere obtenus a partir desdits composes - Google Patents

Composes arylamine reticulables et oligomeres conjugues de polymere obtenus a partir desdits composes Download PDF

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WO2005052027A1
WO2005052027A1 PCT/US2004/035221 US2004035221W WO2005052027A1 WO 2005052027 A1 WO2005052027 A1 WO 2005052027A1 US 2004035221 W US2004035221 W US 2004035221W WO 2005052027 A1 WO2005052027 A1 WO 2005052027A1
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group
occurrence
groups
crosslinkable
polymer
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PCT/US2004/035221
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Scott Gaynor
Michael Inbasekaran
James J. O'brien
Dean M. Welsh
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Sumitomo Chemical Company, Limited
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Priority to DE112004002204T priority Critical patent/DE112004002204T5/de
Priority to GB0611893A priority patent/GB2424897B/en
Priority to US10/579,341 priority patent/US20070096082A1/en
Priority to KR1020067009469A priority patent/KR101196513B1/ko
Priority to JP2006539542A priority patent/JP5209207B2/ja
Priority to CN2004800339570A priority patent/CN1886443B/zh
Publication of WO2005052027A1 publication Critical patent/WO2005052027A1/fr
Priority to US13/683,575 priority patent/US9399702B2/en

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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
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    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Definitions

  • This invention relates to novel crosslinkable arylamine compounds and methods for their preparation.
  • the invention further relates to oligomers and polymers of such compounds, including crosslinked derivatives thereof, as well as films and coatings prepared from such compounds, oligomers or polymers, processes for preparing such films and coatings, and electronic devices, especially electroluminescent devices, comprised of one or more layers of such polymer films.
  • USP's 6,605,373, 6,362,310, 6,255,449, 6,255,447, 6,169,163, 5,962,631 and related patents disclosed certain crosslinkable substituted fluorene compounds and oligomers and polymers therefrom.
  • USP 5,929,194 disclosed the synthesis of polyarylpolyamines by crosslinking of certain small molecule amines containing two reactive groups. Related disclosures are also found in USP 5,728,801. Macromolecular Rapid Communication 21. 583-589(2000) described the synthesis of arylamine containing crosslinkable hole transport materials containing a crosslinkable oxetane group. Macromolecular Rapid Communication 20, 224-228 (1999) described the synthesis of triarylamine small molecules with crosslinkable oxetane groups that can be spin-coated and crosslinked as films. The foregoing references, to the extent crosslinked polymers are disclosed, lack a conjugated polymer backbone, and have only restricted charge transport ability.
  • LED light-emitting diodes
  • High luminosity materials are now available for a large portion of the visible light spectrum, including blue light emitting compounds.
  • a charge transport layer into a multilayer LED between the active or light emitting layer and the anode.
  • Such layers may also be referred to as a hole injection and/or hole transport layer where the purpose is to improve hole injection into the light emitting layer and to provide a buffer layer between the anode and the light emitting layer.
  • the present invention is directed to novel compounds for use in various layers of a multilayer LED, such as hole transport layers and interlayers of a multilayer LED, as well as in other electronic devices such as field effect transistors (FET's), photovoltaic cells, and even for integrated circuits or printed circuit boards.
  • FET's field effect transistors
  • this invention is an arylamine compound of the formula: Z-(Ar-N ) n -Ar-(NX-Ar) n -Z, (I) wherein, Ar independently each occurrence is a group comprising one or more divalent aromatic groups, and optionally two Ar groups separated by a single NX group may be joined together by a second covalent bond or by a bridging group, thereby forming a fused multiple ring system; X is an inert substituent or a cross-linkable group, with the proviso that in at least one occurrence in said compound, X is a crosslinkable group; Z independently each occurrence is hydrogen or a leaving group, n is 1 or 2; and n' is 0, 1 or 2.
  • the compounds of the present invention are capable of forming oligomers and polymers containing relatively large amounts of conjugated unsaturation, thereby resulting in improved charge transport properties. Oligomers and polymers, including copolymers, resulting from crosslinking compositions comprising the foregoing compounds advantageously are characterized by reduced ionization potential and improved conductivity. Moreover, the compounds are capable of forming crosslinked, solvent resistant films that are well suited for use as interlayers in electroluminescent devices.
  • this invention is a composition comprising oligomers, polymers, or crosslinked derivatives thereof having one or more repeating groups of the formula: Z'-(Ar-NX') n -Ar-(NX'-Ar) n .-Z', (la) where X' is X or a divalent crosslinked remnant formed by addition polymerization of a crosslinkable X group, preferably such a group that forms conjugated unsaturation upon crosslinking; Z' is Z, a covalent bond, or a terminal group formed by replacement or reaction of a leaving group; and Ar, X, Z, n and n' are as previously defined with respect to compounds of formula (I).
  • this invention is a process for preparing oligomers, polymers, including copolymers, and crosslinked derivatives thereof comprising one or more groups of formula (la), which process comprises heating one or more compounds of formula (I) or a composition comprising the same, such as a mixture thereof with one or more addition polymerizable monomers, optionally in the presence of any other noninterfering compound, under reaction conditions sufficient to form an oligomer or polymer having one or more repeating groups of Formula (la).
  • this invention is a film comprising one or more of the oligomers or polymers of the second embodiment of this invention or preparable according to the third embodiment of this invention.
  • this invention is an electroluminiscent device comprising one or more layers of polymer films, at least one of which comprises a film according to the fourth aspect of the invention.
  • the foregoing compounds, oligomers and polymers have been discovered to possess especially efficient hole injecting/transporting or electron blocking properties when used to form interlayers in electronic devices, and advantageously are characterized by reduced ionization potential and improved conductivity.
  • the compounds are capable of forming crosslinked, solvent resistant films that are well suited for use as such interlayers in electronic devices such as LEDs.
  • Figure 1 contains electrical properties of the light emitting devices of Example 6.
  • Figures 2 and 3 are DSC scans of the compound of Example 3 A.
  • fused refers to the oligomeric mixture or low molecular weight polymeric mixture resulting from partial polymerization of a monomer. Unreacted monomer may be included in the mixture.
  • Conjugation refers to full or partial overlap of adjacent ⁇ -, p- or d-orbital electrons associated with atoms in the polymer chain of interest.
  • Crosslinkable means a functional group that is capable of being irreversibly cured or polymerized, thereby forming a material that cannot be reshaped or reformed.
  • Crosslinking may be assisted by heat or by UN, microwave, x-ray, or e-beam irradiation. The term is often used interchangeably with "thermosettable" when the crosslinking is done thermally.
  • “Hydrocarbyl” refers to a univalent moiety containing only carbon and hydrogen atoms.
  • Hydrocarbylene refers to a divalent moiety containing only carbon and hydrogen atoms.
  • “Inert substituent” means a substituent group which does not interfere with any subsequent desirable coupling or polymerization reaction of the monomer or oligomer but may include further polymerizable moieties as disclosed herein. Suitable inert non-polymerizable substituents include hydrogen, C ⁇ _ 20 hydrocarbyl and tri(C ⁇ -2 ohydrocarbyl)silyl groups.
  • “Leaving group” means a substituent that is readily displaced or eliminated from the molecule under coupling conditions. Examples of suitable leaving groups include halo, cyano,
  • R 1 independently in each occurrence, is hydrogen or a C M0 alkyl group
  • R 2 independently each occurrence, is a C 2- ⁇ o alkylene group.
  • a preferred leaving group is bromo.
  • crosslinkable X groups are moieties containing a double bond, a triple bond, a precursor capable of in situ formation of a double bond, or a heterocyclic, addition polymerizable group.
  • Preferred crosslinkable X groups include benzocyclobutanyl groups and substituted C 6 - ⁇ 2 arylene groups containing one or more substituents selected from the group consisting of benzocyclobutane, azide, oxirane, di(hydrocarbyl)amino, cyanate ester, hydroxy, glycidyl ether, C ⁇ _ 10 alkylacrylate, CLIO alkylmethacrylate, ethenyl, ethenyloxy, perfluoroethenyloxy, ethynyl, maleimide, nadimide, tri(C 1-4 )-alkylsiloxy, tri(C ⁇ .
  • crosslinkable X groups are l-benzo-3,4- cyclobutane and 4-phenyl-l-(benzo-3,4-cyclobutane).
  • R 3 is hydrogen, halogen, C ⁇ -2 o hydrocarbyl, C ⁇ -20 halohydrocarbyl, or C ⁇ -2 o halocarbyl
  • R 4 is C ⁇ - 20 hydrocarbylene, C ⁇ -2 o halohydrocarbylene, or C ⁇ -2 o halocarbylene
  • p is 0 or 1.
  • X' is either X or a crosslinked remnant of X.
  • crosslinking of an X functional group involves a reaction between two or more X groups in two or more different compounds, oligomers or polymers, or a reaction of an X group with a separately added polymerizable comonomer, thereby joining said molecules into a single chemical entity.
  • X groups comprise an aromatic moiety, preferably a moiety of the formula ArX", wherein Ar is as previously defined and X" is a crosslinkable group having at least one of the crosslink forming atoms thereof covalently bound to an atom of Ar bearing delocalized electronic charge. That is, the X" group is directly attached to an aromatic group comprising Ar.
  • X" groups in this embodiment include 1- ethenyl or benzo-3,4-cyclobutan-l-yl groups, and inertly substituted derivatives thereof.
  • the X" groups are self-crosslinkable, meaning that no initiator, such as an acid, base or peroxide compound, is needed to initiate crosslinking involving said X" group, it being understood that copolymerizable comonomers, especially addition polymerizable comonomers such as ethylenically unsaturated compounds, may additionally be present.
  • Suitable inert, non-crosslinkable, X groups include C ⁇ -2 o hydrocarbyl and halogenated C ⁇ . 20 hydrocarbyl groups, especially aryl and alkaryl groups.
  • Preferred non-crosslinkable X groups include phenyl and C MO alkylphenyl, especially p-n-butylphenyl.
  • Suitable Ar groups include phenylene, biphenylene, naphthalenediyl, anthracenediyl, stilbenediyl, and fluorenediyl groups, inertly substituted derivatives thereof, and combinations of the foregoing groups.
  • Preferred fluorenediyl groups correspond to the formula:
  • R' independently each occurrence, is an inert substituent, X or X'.
  • R' independently each occurrence, is an inert substituent, X or X'.
  • two Ar groups separated by a single -NX- group may form a fused aromatic ring system. Examples include groups corresponding to the formulas:
  • X is as previously defined; Y is a covalent bond, O, S or NR; where R independently in each occurrence is i) hydrogen; ii) halogen; iii) a C ⁇ -2 o hydrocarbyl group; iv) a hydrocarbyl group substituted with one or more heteroatom containing groups containing up to 20 atoms not counting hydrogen and wherein the heteroatom is selected from S, N, O, P, B or Si; v) a halogenated derivative of iii) or iv); or vi) a substituted derivative of iii) or iv) wherein the substituent is a crosslinkable X group.
  • Preferred substituents, R include Cr -40 hydrocarbyl groups or C 1-40 hydrocarbyl groups containing one or more S, N, O, P, or Si heteroatoms, and the foregoing C ⁇ - 0 hydrocarbyl or C 1-40 heteroatom containing groups substituted by a crosslinkable X group.
  • Ris a C ⁇ -10 alkyl group.
  • the monomers, oligomers and polymers of the invention preferably are highly conjugated, if not completely conjugated, along the backbone defined by -(Ar-NX') n -Ar-(NX'-Ar) n -.
  • the crosslinked oligomers and polymers of the invention are also highly conjugated, if not completely conjugated, along the crosslinked structure defined by at least one: — Ar — X' group.
  • n, n', R, X, Y and Z are as previously defined.
  • Specific examples of the oligomers and polymers of formula la) according to the present invention are those having the following structures:
  • n, n', R, X', Y and Z' are as previously defined.
  • Such oligomers and polymers are readily prepared using conventional synthetic techniques to cause loss or polymerization of the leaving group, Z, and formation of the remnant, Z'. Suitable techniques include the well known Buchwald or half-Buchwald reaction, Suzuki coupling reactions, or similar techniques. The oligomers and polymers are highly suited for use in the preparation of both hole transport films and interlayer films in electroluminiscent devices.
  • the arylamine compounds of formula T) or la) of the invention are readily polymerized to form crosslinked oligomers or polymers by heating a composition comprising such compound at an elevated temperature for a time sufficient to result in addition polymerization or other crosslinking reaction of at least some X functionality.
  • Li one embodiment the compounds are copolymerized with one or more copolymerizable monomers capable of forming divalent crosslinking moieties.
  • Preferred copolymerizable compounds for use herein correspond to the formulas (IT) or ( ⁇ J):
  • Q 1 is independently in each occurrence C ⁇ . 2 o hydrocarbyl or C 1-2 o hydrocarbyl containing one or more S, N, O, P or Si atoms, C . ⁇ 6 hydrocarbyl carbonyloxy, C 4- i 6 aryl(trialkylsiloxy) or both Q 1 may form with the 9-carbon on the fluorene ring a C 5-2 o ring structure or a C 4-20 ring structure containing one or more of S, N or O; Q 2 is independently in each occurrence C 1-2 o hydrocarbyl, C 1-2 o hydrocarbyloxy, Cj.
  • thioether C 1-2 o hydrocarbylcarbonyloxy or cyano
  • Q is independently in each occurrence C 1-2 o hydrocarbyl or C 1-20 hydrocarbyl substituted with di(C 1-20 alkyl)amino, C 20 hydrocarbyloxy or C 1-20 hydrocarbyl or tri(C 1-10 alkyl)siloxy
  • a is independently in each occurrence 0 or 1
  • Z" is a leaving group, especially bromo.
  • the oligomers and polymers of the invention comprise from 1 to 99 percent, more preferably from 2 to 50 percent, and most preferably from 2 to 10 percent of repeat units of formula la) and 99 to 1 percent, more preferably 98 to 50 percent, most preferably 98 to 90 percent of repeat units of the formula:
  • the monomers and oligomers or b-staged derivatives of the invention are readily soluble in common organic solvents. They are processible into thin films or coatings by conventional techniques, particularly solution spin coating or ink-jet printing, with or without the use of a solvent.
  • the oligomers or polymers of this invention preferably have a weight average molecular weight of 1000 Daltons or greater, more preferably 5000 Daltons or greater, even more preferably 10,000 Daltons or greater, highly preferably 15,000 Daltons or greater and most preferably 20,000 Daltons or greater; preferably 1,000,000 Daltons or less, more preferably 500,000 Daltons or less and most preferably 200,000 Daltons or less.
  • Molecular weights are determined by use of gel permeation chromatography using polystyrene standards.
  • the degree of polymerization of the polymers of the invention as measured by the number of repeat units therein is preferably at least 2, more preferably at least 3.
  • the oligomers or polymers demonstrate a polydispersity (Mw/Mn) of 5.0 or less, more preferably 3.0 or less, and most preferably 2.0 or less.
  • Processes for Preparing Oligomers or Polymers The compounds, oligomers and polymers of the invention are prepared by any suitable process, including a condensation reaction of an aromatic boronate and a bromide, commonly referred to as the "Suzuki reaction", as reported by N. Miyaua and A. Suzuki in Chemical Reviews. Vol.
  • This palladium catalyzed reaction can be applied to preparing high molecular weight polymers and copolymers with addition of a phase transfer catalyst as taught in US-A-5,777,070.
  • the reaction is typically conducted from 70°C to 120°C in suitable solvent or diluent.
  • suitable solvents include aromatic hydrocarbons, such as toluene or diethylbenzene, or aliphatic or aromatic ethers, esters, or carbamates, such as tetrahydrofuran or dimethylformamide. Mixtures of the foregoing solvents or diluents may be employed as well.
  • a most preferred solvent is toluene.
  • An aqueous base preferably sodium carbonate or bicarbonate, is used as a scavenger for the reaction product of the leaving group, generally HBr.
  • a polymerization reaction may take from 1 minute to 100 hours.
  • a monofunctional aryl halide or an aryl boronate compound may be added as a chain-terminator in such reactions, thereby resulting in the formation of a terminal aryl group.
  • Polymerization processes involving only dihalo-functional reactants used in the formation of compounds according to the present invention may also be carried out using nickel catalyzed coupling reactions. One such coupling reaction was described by Colon et al.
  • nickel-catalyzed coupling reaction was disclosed by Yamamoto in Progress in Polymer Science. Vol. 17, p. 1153 (1992) wherein a mixture of dihaloaromatic compounds were treated with an excess amount of nickel (1,5-cyclooctadiene) complex in an inert solvent. All nickel-catalyzed coupling reactions when applied to reactant mixtures of two or more aromatic dihalides yield essentially random copolymers. Such polymerization reactions may be terminated by the addition of small amounts of water to the polymerization reaction mixture, thereby replacing the terminal halogen groups with hydrogen groups. Alternatively, a monofunctional aryl halide may be used as a chain-terminator, resulting in the formation of a terminal aryl group.
  • the polymers of the invention desirably contain conjugated unsaturated groups.
  • Conjugated groups refers to moieties containing two or more double bonds, triple bonds and/or aromatic rings, separated by a single covalent bond. The incorporation of such groups into the polymer may be used to modify the light absorption, ionization potential, and/or electronic properties of the polymer.
  • Preferred unsaturated groups present in the conjugated unsaturated group- containing comonomers for use herein include divalent derivatives of hydrocarbons such as divalent derivatives of benzene, naphthalene, acenaphthene, phenanthrene, anthracene, fluoranthene, pyrene, rubrene, and chrysene, as well as unsaturated heterocyclic groups, such as divalent derivatives of furan, thiophene, pyrrole, oxazole, isooxazole, thiazole, isothiazole, imidazole, oxadiazoles, thiadiazole, pyrazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, tetrazene; benzoxazole, benzothiazole, benzimidazole, quinoline, isoquinoline, cinnoline, quinazoline
  • Highly desirable copolymerizable conjugated unsaturated groups include 9,9-disubstituted fluorenediyl groups and triarylamine groups. It is possible to control the sequencing of the monomeric units in the resulting copolymers by controlling the order and composition of monomer feeds, especially when employing a Suzuki reaction.
  • a high molecular weight copolymer comprising mainly large blocks of polyfluorenediyl homopolymers connected to short blocks of alternating diarylamine-comonomer oligomers may be made by first introducing into the reaction suitable reactants in the appropriate ratio to make the alternating fluorenediyl-comonomer oligomers followed by the remainder of diarylamine monomers so long as there is an overall stoichiometric balance of the reagents, that is, the boron and bromine containing reagents.
  • diarylamine groups that may be additionally incorporated into the copolymers of the invention are tertiary aromatic amines containing two reactive substituents.
  • Such compounds result in the inclusion of the corresponding triarylamine remnant into the copolymer.
  • suitable tertiary aromatic amines include, triphenyl amine, al yldiaryl amines, N,N,N',N'-tetraphenylbenzidine, and N,N,N',N'-tetraphenyl-l,4-phenylenediamine.
  • copolymerizable, conjugated compounds containing up to 60 carbons are useful for the present purpose. They may be substituted optionally with one or more substituents that are not deleterious to the photoluminescent properties of the polymer compositions.
  • substituents include -C 20 hydrocarbyl radicals, C 1 -C 20 (thio)alkoxy radicals, C ⁇ -C 2 o (thio)aryloxy radicals, cyano, fluoro, chloro, C ⁇ -C 2 o alkoxycarbonyl, C C o aryoxylcarbonyl, C 1 -C 20 carboxyl and alkyl(aryl)sulfonyl radicals.
  • substituents which are known photoluminescent quenchers, such as arylcarbonyl and nitro groups, are undesirable and should be avoided.
  • the oligomers and polymers of invention may be used in forming a blend of at least two polymers. If desired, one or more of the oligomers or polymers of the blend may be a light- emitting polymer.
  • the blend is composed of one or more polymeric materials selected from polystyrene, polybutadiene, poly(methyl methacrylate), poly(ethylene oxide), phenoxy resins, polycarbonates, polyamides, polyesters, polyurethanes, polyimides, crosslinked epoxy resins, crosslinked phenolic resins, crosslinked acrylate resins, and crosslinked urethane resins. Examples of these polymers may be found in Preparative Methods of Polymer Chemistry. W. R. Sorenson and T. W.
  • the blends comprising a crosslinked polymer are formed by blending the uncrosslmked components and later crosslinking the components in situ.
  • the blend comprises at least two light emitting polymers and the maximum emission wavelength of one of the polymers in the blend is within 25 nm of the maximum absorption wavelength of at least one other polymer in the blend.
  • the blend comprises a mixture of two polymers each corresponding to the present invention in the range from 0.1 to 99.9 and 99.9 to 0.1 percent respectively.
  • the primary use for the oligomers and polymers of the invention is in the formation of films.
  • films can be used in preparing photoluminescent or fluorescent coatings as well as interlayers, protective coating, and hole transport layers in electronic devices such as organic light emitting diodes, especially polymeric light-emitting diodes, photovoltaic cells, lighting, photodiodes, sensors, thin film transistors, and other devices.
  • the thickness of the coating or film is dependent upon the ultimate use. Generally, such thickness can be from 0.01 to 200 micrometers. When used as a fluorescent coating, the film thickness is desirably from 50 to 200 micrometers. When used as electronic protective layers, the film thickness is desirably from 5 to 20 micrometers.
  • the film thickness is desirably from 0.001 to 2 micrometers.
  • the oligomers or polymers of the invention form films that are substantially lacking in pinholes and other defects.
  • Such films can be prepared by means well known in the art including spin-coating, spray-coating (including ink-jet spraying), dip- coating and roller-coating.
  • Such coatings are prepared by a process wherein a composition comprising the present compounds, oligomers or polymers is applied to a substrate and exposed to conditions such that a film is formed, generally by means of a crosslinking reaction. The conditions which form a film depend upon the application technique and the reactive end groups of the film forming moieties.
  • the solution contains from 0.1 to 10 weight percent of the oligomers or polymers of the invention, and the remainder solvent.
  • the composition contains from 0.5 to 5.0 percent by weight of the compounds, oligomers or polymers.
  • This composition is then applied to the appropriate substrate by the desired method and the solvent is allowed to evaporate. Residual solvent may be removed by vacuum and or by heat. If the solvent is low boiling, then low solution concentrations, for example, 0.1 to 2 percent, are desired. If the solvent is high boiling, then high concentrations, for example, 3 to 10 percent, are desired. After removal of the solvent, the coating is then exposed to the necessary conditions to cure the film, if needed, thereby preparing a film having high solvent and heat resistance.
  • the films are preferably substantially uniform in thickness and substantially free of pinholes.
  • the films are cured when exposed to temperatures of 100°C or greater, more preferably 150°C or greater and most preferably 200°C or greater.
  • the films cure at a temperature of 300°C or less.
  • the composition may further comprise a catalyst suitable to facilitate or initiate the crosslinking process.
  • a catalyst suitable to facilitate or initiate the crosslinking process are well known in the art, for instance, for materials having ethylenic unsaturation, a free radical catalyst may be used.
  • a free radical catalyst may be used for aryl moieties with glycidyl ethers as end-groups.
  • ureas or imidazoles may be used.
  • the materials may be reacted with commonly known curing agents which facilitate crosslinking.
  • curing agents are tetrahydrophthalic anhydride, methylbicyclo[2.2.1]heptane- 2,3-dicarboxylic anhydride (nadic anhydride), and maleic anhydride.
  • the monomers and oligomers may be partially cured or
  • the composition is exposed to conditions such that a portion of the reactive materials cure and a portion of the reactive materials do not cure. This is commonly used to improve the handleability of composition and can facilitate the preparation of films.
  • Such B-staged material can thereafter be used to prepare coatings by the means disclosed above. Preferably, from 10 to 50 percent of the reactive moieties are reacted during B-staging.
  • Yet another aspect of the invention relates to organic electroluminescent (EL) devices comprising a film of the polymers of this invention.
  • An organic EL device typically consists of an organic film located between an anode and a cathode in electrical contact therewith, such that when a positive bias is applied to the device, holes are injected into the organic film from the anode, and electrons are injected into the organic film from the cathode. The subsequent combination of a hole with an electron may give rise to an exciton which may undergo radiative decay to the ground state by liberating a photon.
  • the anode is commonly a mixed oxide of indium and tin (ITO), employed for its high conductivity and transparency. The mixed oxide is normally deposited on a transparent substrate such as glass or plastic so that the light emitted by the organic film may be observed.
  • ITO indium and tin
  • the organic film may be the composite of several individual layers each designed for a distinct function or purpose. Since holes are injected from the anode, the layer next to the anode desirably has suitable functionality for transporting holes. Similarly, the layer next to the cathode desirably has suitable functionality for transporting electrons. In many instances, the hole or electron transporting layer also acts as the emitting layer. In some instances, one layer performs the combined functions of hole transport, electron transport, and light emission. Generally, films comprising the polymers of the present invention act as buffer layers or hole transport layers in an electronic device. In addition to the foregoing polymeric film layers, films of small molecules deposited by thermal evaporation may be incorporated into the electronic device, if desired.
  • the total thickness of the organic film be less than 1000 nm, more preferably less than 500 nm, most preferably less than 300 nm.
  • One embodiment of the instant invention is an EL device in which the organic film comprises at least one of the polymeric compositions of this invention.
  • the ITO surface which serves as the anode may be coated with a film according to the invention usually after first cleaning the exposed surface with an aqueous detergent solution, an organic solvent, and/or a UV or plasma generated ozone treatment. It may also be coated with a thin layer of a conducting substance to facilitate hole injection if desired.
  • Suitable conducting substances include copper phthalocyanine, polyaniline and poly(3,4-ethylenedioxy-thiophene) (PEDT); the last two of which in their conductive forms are prepared by doping with a strong organic acid, for example, poly(styrenesulfonic acid). It is preferred that the thickness of the conducting layer, when used, be 200 nm or less; more preferably 100 nm or less.
  • the present compounds may be used in the preparation of interlayers in a multilayer device or as one component of a mixture of compounds forming a hole transporting polymer layer or as a separate hole transporting layer in a multilayer electronic device, especially an electroluminiscent device.
  • hole-transporting polymer other than the present invention known hole-conducting polymers, such as polyvinylcarbazole, or the polymeric aryl amines disclosed in USP's 5,728,801 or 5,929,194 may be employed.
  • the resistance of this layer to erosion by the solution of the copolymer film which is to be applied next is obviously critical to the successful fabrication of multi-layer devices. Accordingly the copolymers of this invention are normally applied from solutions in organic solvents such as xylene or toluene in which the hole-transporting layer is insoluble.
  • the hole-transporting polymer By covering or protecting the hole-transporting polymer with an interlayer comprising a crosslinked polymer according to the present invention, the hole-transporting polymer can be protected from subsequent reagents or solvents employed in manufacture of the electronic device.
  • the thickness of the hole-transporting layer or interlayer according to the invention is desirably 500 nm or less, preferably 300 nm or less, most preferably 150 nm or less.
  • a suitable electron-transporting layer, if used, may be applied either by thermal evaporation of a low molecular weight material or by solution coating of a polymer, such as a polymer according to the present invention, using a solvent that does not significantly damage any previously deposited film layer.
  • Examples of low molecular weight materials conventionally used in forming electron-transporting layers include metal complexes of 8-hydroxyquinoline (as described by Burrows et al. in Applied Physics Letters. Vol. 64, pp. 2718-2720 (1994)), metallic complexes of 10-hydroxybenzo(h)quinoline (as described by Hamada et al. in Chemistry Letters. pp. 906-906 (1993)), 1,3,4-oxadiazoles (as described by Hamada et al. in Optoelectronics - Devices and Technologies. Vol. 7, pp. 83-93 (1992)), 1,3,4-triazoles (as described by Kido et al. in Chemistry Letters, pp.
  • Polymeric electron-transporting materials in addition to those of the present invention are exemplified by 1,3,4-oxadiazole-containing polymers (as described by Li et al. in Journal of Chemical Society, pp. 2211-2212 (1995), by Yang and Pei in Journal of Applied Physics. Vol 77, pp. 4807-4809 (1995)), 1,3,4-triazole-containing polymers (as described by Strukelj et al. in Science, Vol. 267, pp.
  • the thickness of this layer may be 500 nm or less, preferably 300 nm or less, most preferably 150 nm or less.
  • the final layer in the electronic device is normally the cathode, which may be formed from any conductive material, preferably a metal.
  • suitable metals include lithium, calcium, magnesium, indium, silver, aluminum, or blends and alloys of the above.
  • a metallic cathode may be deposited either by thermal evaporation or by sputtering, according to known techniques. The thickness of the cathode may be from 100 nm to 10,000 nm.
  • the preferred metals are calcium, magnesium, indium, and aluminum. Alloys of these metals may also be used. Alloys of aluminum containing 1 to 5 percent of lithium and alloys of magnesium containing at least 80 percent magnesium are highly preferred.
  • the EL devices of this invention emit light when subjected to an applied voltage of 50 volts or less with luminance efficiency as high as 3.5 Cd/A.
  • the electroluminescent device comprises at least one hole- transporting polymer film and a light-emitting polymer film at least one of which is comprised of a polymer of the invention, arranged between an anode material and a cathode material such that under an applied voltage, holes are injected from the anode material into the hole-transporting polymer film and electrons are injected from the cathode material into the light-emitting polymer films when the device is forward biased, resulting in light emission from the light-emitting layer.
  • layers of hole-transporting polymers are arranged so that the layer closest to the anode has the lower oxidation potential, with the adjacent layers having progressively higher oxidation potentials.
  • electroluminescent devices having relatively high light output per unit voltage may be prepared.
  • hole-transporting polymer film refers to a layer of a film of a polymer which when disposed between two electrodes to which a field is applied and holes are injected from the anode, permits adequate transport of holes into the emitting polymer.
  • light-emitting polymer film refers to a layer of a film of a polymer whose excited states can relax to the ground state by emitting photons, preferably corresponding to wavelengths in the visible light range.
  • anode material refers to a semi-transparent, or transparent, conducting film with a work function between 4.5 electron volts (eV) and 5.5 eV. Examples are gold and oxides and mixed oxides of indium and tin.
  • cathode material refers to a conducting film desirably having a work function between 2.5 eV and 4.5 eV.
  • X is an inert substituent or a cross-linkable group, with the proviso that in at least one occurrence in said compound, X is a crosslinkable group;
  • Z independently each occurrence is hydrogen or a leaving group, n is 1 or 2; and n' is 0, 1 or 2.
  • a compound according to embodiment 1 wherein X in at least one occurrence is a moiety containing a double bond, a triple bond, a precursor capable of in situ formation of a double bond, or a heterocyclic, addition polymerizable group.
  • a compound according to embodiment 1 wherein X in at least one occurrence is selected from the group consisting of benzocyclobutanyl groups and substituted C 6 - ⁇ 2 arylene groups containing 1 one or more substituents selected from the group consisting of 'benzocyclobutane, azide, oxirane, di(hydrocarbyl)amino, cyanate ester, hydroxy, glycidyl ether, C ⁇ -4 alkylacrylate, l '
  • X is 3,4-benzocyclobutan-l-yl, ethenyl or p-ethenylphenyl;
  • Z is bromine or hydrogen;
  • n is 1 or 2; and
  • n' is 0 or 1.
  • Y is a covalent bond, O, S or NR; where R independently each occurrence is i) hydrogen; ii) halogen; iii) a C ⁇ -2 o hydrocarbyl group; iv) a hydrocarbyl group substituted with one or more heteroatom containing groups containing up to 20 atoms not counting hydrogen and wherein the heteroatom is selected from S, N, O, P, B or Si; v) a halogenated derivative of iii) or iv); or vi) a substituted derivative of iii) or iv) wherein the substituent is a crosslinkable X group; and In, n', X, and Z are as previously defined in embodiment 1.
  • X' is X or a divalent crosslinked remnant formed by addition polymerization of a crosslinkable X group;
  • X is an inert substituent or a group capable of forming crosslinking functionality;
  • Y is O, S or NR';
  • R independently each occurrence is i) hydrogen; ii) halogen; iii) a C 1-2 o hydrocarbyl group; iv) a hydrocarbyl group substituted with one or more heteroatom containing groups containing up to 20 atoms not counting hydrogen and wherein the heteroatom is selected from S, N, O, P, B or Si; v) a halogenated derivative of iii) or iv); or vi) a substituted derivative of iii) or iv) wherein the substituent is a crosslinkable X group;
  • Z' is Z, a covalent bond or a terminal group formed by replacement or reaction of a leaving group;
  • n is 1 or 2; and
  • a crosslinked polymer according to embodiment 10 or 11 wherein X' in at least one occurrence is a divalent crosslinked remnant formed by addition polymerization of a crosslinkable X group.
  • a film comprising one or more of the oligomers or polymers according to embodiment 10 or preparable according to embodiment 14.
  • An electronic device comprising one or more layers of polymer films, at least one of which comprises a film according to embodiment 15.
  • reaction scheme 1 discloses the preparation of a triaryl amine compound with a crosslinkable benzocyclobutane group and its use in a polymerization reaction to make a crosslinkable amine copolymer according to the invention containing 5 mole percent crosslinkable conjugated diaryl amine functionality and 95 mole percent noncrosslinkable diarylamine functional units.
  • N-bromosuccinimide N-bromosuccinimide (NBS, 10.5 g, 60.7 mmol, 1.97 eq.) is added. After stirring for 5 hours, the reaction is quenched by pouring the reaction mixture into 600 ml of methanol/water (1 : 1 by vol). A gray solid is recovered by filtration and recrystallized from isopropanol. *H NMR (CDCl 3 -d) ⁇ : 7.3 (d, 4H, Ar), 7.0 (d, 4H, Ar), 6.95 (t, Ar), 6.8 (s, Ar), 3.12 (d, 4H, -CH 2 CH 2 -).
  • Example 3 Scheme 2 shows the synthesis of a phenylenediamine monomer with a crosslinkable benzocyclobutane group, and the polymerization reaction used to make a fluorene/amine copolymer containing 5 mole percent of crosslinkable moieties able to achieve conjugated crosslinks.
  • N,N'-diphenyl-l,4-phenylenediamine (10.0 g, 38.4 mmol), bromobenzocyclobutane (15.5 g, 76.8 mmol) and 200 ml toluene are added, followed by sodium t-butoxide (7.37 g, 76.8 mmol).
  • sodium t-butoxide 7.37 g, 76.8 mmol.
  • the reaction is heated to reflux under nitrogen for 22 hours.
  • the reaction is quenched by addition of 30 ml of 1 M aqueous HC1.
  • the toluene solution is passed through basic alumina and the crude product is purified by recrystallization from a toluene/hexanes/methanol mixture.
  • Example 5 Crosslinked Films A) The crosslinkable monomers of Examples 2 and 4 are dissolved in 4 ml of mixed xylenes. The solutions are shaken at room temperature overnight and then filtered through a 0.45 ⁇ m nylon syringe filter. On a cleaned glass substrate, a cured film of about 80 nm thickness is deposited by spin-coating each solution at 4000 rpm. The films are then heated in a nitrogen- filled oven at 250 °C for 30 min. to create crosslinking in the film. The UV-Vis absorption spectra of the films are measured. The films are then rinsed with toluene, rinsed and dried and the absorption spectra remeasured.
  • Example 6 Light emitting device using crosslinked and uncrosslinked films as interlayers
  • a conventional hole transport layer polymer (Baytron PTM, available from Sigma-Aldrich Corporation) is spin coated on a cleaned ITO substrate to a thickness of 80 nm and cured in air at 200 °C for 15 minutes.
  • a filler layer of the crosslinkable polymer from Example 2 is similarly deposited from xylenes (0.5 % w/v) and cured (crosslinked) for 30 minutes at 250 °C in a nitrogen atmosphere.
  • a light emitting polymer prepared substantially according to the teachings of USP 6,353,083 is spin-coated from a solution in xylenes (1.5 % w/v) and cured at a temperature of 130 °C.
  • the cathode metals (Ca, 10 nm and Al, 150 nm) are vapor deposited over the resulting polymer film.
  • the foregoing procedures are substantially repeated to produce light emitting diodes having no interlayer (comparative) and a dried but uncured (uncrosslmked) interlayer. Electroluminescent properties of the light emitting diodes are then tested. Results are reported in Figure 1.

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Abstract

Cette invention concerne des composés arylamine réticulables, des oligomères et des polymères obtenus à partir de tels composés; des films et des revêtements ; et des dispositifs électroniques multicouches comprenant de tels films.
PCT/US2004/035221 2003-11-17 2004-10-25 Composes arylamine reticulables et oligomeres conjugues de polymere obtenus a partir desdits composes WO2005052027A1 (fr)

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DE112004002204T DE112004002204T5 (de) 2003-11-17 2004-10-25 Vernetzbare Arylaminverbindungen und darauf basierende konjugierte Oligomere oder Polymere
GB0611893A GB2424897B (en) 2003-11-17 2004-10-25 Crosslinkable arylamine compounds and conjugated oligomers or polymers based thereon
US10/579,341 US20070096082A1 (en) 2003-11-17 2004-10-25 Crosslinkable arylamine compounds and conjugated oligomers or polymers based thereon
KR1020067009469A KR101196513B1 (ko) 2003-11-17 2004-10-25 가교성 아릴아민 화합물 및 이를 기재로 한 공액 올리고머또는 중합체
JP2006539542A JP5209207B2 (ja) 2003-11-17 2004-10-25 架橋性アリールアミン化合物、及びそれをベースにしたポリマーの共役オリゴマー又はポリマー
CN2004800339570A CN1886443B (zh) 2003-11-17 2004-10-25 可交联的芳基胺化合物和基于它们的共轭低聚物或聚合物
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